30 Day OTP Challenge, Contestshipping
by AbigailJonesNY
Summary: 30 lovey-dovey-fluffy prompts. May and Drew. What could be better! Rated T for future chapters!
1. Holding Hands

**Day 1: Holding Hands**

"Dreeeeew!" May shouted. Said green-haired boy looked behind himself at the brunette barreling toward him. She stopped about a foot away from him, her grin growing wider. "You did great today during the contest! I didn't know if Glaceon and I could beat you!" she giggled. Drew smirked, rolling his eyes.

"Whatever, May. I let you win that one and you know it." Drew tossed his arms up, crossing them over the back of his head. Roserade looked up at her trainer in confusion. She lifted one flowery hand to his side, nudging him as if to tell him not to lie like that.

May laughed, noticing the gesture. "Looks like even Roserade knows better than that, Drew," she snickered. Drew blushed, glaring at his partner pokemon. "It's ok, we've both changed with battling, and I've just gotten a lot stronger. Maybe even stronger than you~!" May teased. Drew turned his head away, huffing and crossing his arms over his chest.

"Whatever, May." He mumbled. He was acting quite babyish about the whole thing. Hm…

The brunette smirked and took his hands, keeping only inches between their faces. Drew gave her his attention back, how could he not? "Rematch later?"

The green-haired boy gulped but nodded nonetheless. May giggled, throwing their hands up and spinning around, forcing the shocked Drew to copy. "Seeya later, Drew!" May released his hands and ran down the dirt road toward the Pokemon Center.

Drew stood stiff for a minute, taking in everything that had just happened. His usual smirk came back, and with a flip of his hair, he started down the road calmly with Roserade beside him.

"Ro…"

That did it.

"SHE'S CUTE, OKAY?!" Drew squealed. "She was holding my hands, spinning me around, we were close enough to kiss, do you realize how great that could've just been?! No of course not…you've gotta calm down Drew…deep breaths…" he paused, his pokemon looking at him as if he were completely insane. "IT'S NOT WORKIIIIING!" he squealed again. Man, that is only cute for a minute…

**HIIIII! This is my first Pokemon fic, so bare with me. Contestshipping was one of the first things I ever shipped so it holds a special spot in my heart. I may not update this every day (like I'm supposed to...) but I'll try! Also, this is set post-Ash and Brock in case you couldn't tell. **

**Tomorrow's Prompt- Cuddling Somewhere.**

**Review and tell me what you think of this so far!**


	2. Cuddling Somewhere

**Day 2: Cuddling Somewhere**

The Pokemon Center was full, to say the least. With the approaching storm and contest, it was no wonder Nurse Joy was doubling up people in the bedrooms. Of course, May got lucky enough to get Drew. Can you hear the sarcasm?

She sighed, dumping her bag in a chair and standing by the sliding doors that led out onto the balcony. She heard the door open behind her, though she knew who it was and didn't even bother turning her head to look. "Hey, May," Drew greeted and flopped onto the bed. May rolled her eyes when she heard the TV flick on.

"Spongebob, really?" She turned around and crossed her arms at her rival.

"It's just funny when they mess up and show how stupid they are." Drew said, laying the remote by his side to cross his arms behind his head. May laid on the other half of the bed and stole the remote, pulling up the guide.

"I'm not watching Spongebob," she said as she searched for something better on. _Dumb…lame…boring…seen it…seen it five times…dumb…oh!_ May stopped on _Cyberbully_, something she hadn't seen! Finally!

"Ummm…May, you may not wanna watch this…" Drew warned, noticing the title before it faded off.

"And why not? Just because it's not dumb or violent?"

"It's actually more violent than you think…"

May huffed, turning up the volume just to spite him. "Fine, but don't say I didn't warn you…" May stuck her tongue out at the green haired boy.

* * *

May's face was red-hot with huge tears falling faster than the rain outside. She hiccupped every few seconds, her face buried in her knees. She didn't even finish the movie, switching it off when Taylor found the pills. She didn't want to see the end. No way. Drew had fallen asleep, not even flinching when May gasped for air in her cries.

"Dr-Drew…D-Drew!" she smacked at him lightly, her shaking hands balled into weak fists. Drew rolled over slowly then became aware of the crying and soundless television.

He sat right up, "You ok, May?" The brunette tried to nod and wipe at her tears, hiccups still persisting. Drew bit his lip before pulling her closer and snatching the remote.

"N-no! I-I don't w-wanna see the e-end!" May cried.

"Yes you do…" Drew mumbled, rubbing her back comfortingly. They finished out what was left- about ten minutes- and May calmed down. "Little bit cliché in the end, huh?" Drew tried to joke. May looked up at him, a few stray tears still journeying down her face. He wiped them away and pecked the top of her head, rubbing her shoulders.

"Th-thanks, Drew…" May said quietly.

"Ah, it's nothing…" he smirked. "I don't think you'd have let me sleep unless you knew what happened." He laid back down and shut his eyes, fighting the grin that wanted to show.

"Humph!" May crossed her arms dramatically, turning her nose up at him. "Jerk!" she whined. Drew pulled her arm, yanking her down on the other pillow before wrapping an arm around her and falling back asleep.

"You know you love me…" he mumbled.

"Whatever…" May rolled her eyes but faced him as she drifted off to sleep.

**First off, me no own-y **_**Spongebob**_** or **_**Cyberbully**_**. But man is that movie saaaaaaad!**

**Also, thank you if you've reviewed! It means a lot to me when I get reviews and love and a;lksdjf;l! **

**Tomorrow's prompt: Gaming/Watching a movie. Since I already had them watch a movie to initiate the cuddles, they will be gaming. Any ideas on what game they should play, guys?**

**Review and tell me what you thought!**


	3. GamingWatching a movie

**Day 3: Gaming/Watching a movie**

The rain shower was still going on, passing its fourth day. May was growing anxious after having been cooped up inside for such a long amount of time, and was willing to do anything to get her mind off of her cabin fever.

Drew, on the other hand, was having no problem with being inside. It was a relaxing break from being on the road. He was busy showering; well more like drying considering the water had stopped. May was sprawled out on the bed, staring at the ceiling and finding different faces and shapes when he walked out, towel drying his hair.

"What are you doing?" he asked. May dropped her arm from its drawing position, sitting up just to see Drew in something she'd never had imagined he could own: sweatpants and a black t-shirt with the _Spiderman_ logo.

"A better question would be what are you _wearing_?" she giggled. Drew blushed slightly, tossing the towel into a clothes hamper.

"They're pajamas, so hush," he responded. "But, seriously, why were you tracing the ceiling?"

May sighed exaggeratedly, "I'm so freaking booooored! We've been inside for _four days straight_." She flopped back on the bed, kicking her feet childishly.

"It's not that bad, May." Drew started, "But, if you're that bored, we could always play a video game?" he suggested, sitting on one corner of the bed while the brunette whined and squirmed. "There's a Wii set up downstairs, we can go play on that."

May nodded, launching herself up off the bed. "Race ya down there!" she giggled, zooming down the stairs.

* * *

They picked a game, Mario Kart, and got the controllers they needed. Each in a chair, they selected the race and karts. They'd be racing against each other for the Star Cup; May with Dry Bones and Drew with Yoshi.

"Shall we make it interesting?" May suggested, a smirk present on her face.

Drew faced her, the spark of competition lighting up his eyes. "What do you propose?" he asked.

"How about if you lose I get to paint your nails…!"

"…Alright. But when I win, you have to…give me a kiss." Drew responded, keeping an emotionless face.

"Wh-what! No way!" May blushed, scooting back. "I'm not kissing you, Drew!"

"So you think you'd lose no matter what?" Drew smirked.

May scowled, turning back to the television, "Fine. But I'm not losing!" she announced, pressing 'start' on the screen. The two raced through Daisy Circuit, May claiming a win. Then passed Koopa Cape and Maple Treeway with Drew taking the victories.

"Only one more round, May. Wanna just go ahead and give up?" Drew snickered.

May huffed, her eyes locking on the screen, "No way! I could still win this race!" she shouted, smacking the 'A' button to start the race. They flew out of the start, ducking into the cave with Drew smacking at May's kart. They passed the line with May in first and Drew in second, only to pass her into first with the assistance of a blue shell. Lap 2 had Drew in the lead. "Look out behind you~!" May sang before a red shell collided into the back of Drew's kart, allowing May to pass him and take the race.

The score came up, marking May in first place for the race and Drew in second. Total scores came up and the two tied. "Well, looks like neither of us won, the bet is null and void!" May laughed.

"Well, we could always do a time trial and decide the winner from that?" Drew said. May looked back at the TV, she knew what she could do if she won, which she just proved she could do. With a nod, they picked Rainbow Road and were off. They both fell numerous times, surprised by bounces off the rails and misjudging the distance over the circles in the middle of the road. Finally, they came to a stop and Drew whirled passed the line, barely making it into first place. "WOOHOO!" he cheered, throwing his hands up and feet out.

May sat frozen, _I lost…I have to kiss Drew…_ Her eyes widened and she whined, throwing herself back against the seat. "Nooooo!" she kicked.

"Maaaaay," the green haired boy drew out, flicking his hair coolly. "I think you owe me something." He was trying his hardest to contain his excitement, though it showed somewhat in his eagerness to get that kiss.

"Do I have to?" May asked, knowing what he was going to say.

"Well, you lost and you agreed to the bet…yep. You have to." He smirked. Even though that smirk turned into more of a goofy smile.

May sighed and stood up, crossing the short distance between her and Drew, "Fine…" Drew stood and May leaned down to him, quickly pecking his lips. "H-happy?" she blushed. Drew's face grew even warmer than hers, the red almost as bright as a rose. He nodded and coughed into his hand.

"W-wanna race again?"

**I don't own _SpiderMan _or Mario Kart! That's pretty obvious but ya know...bleh.**

**Tomorrow's prompt: On a date. Hehehe...**

**Review and tell me what you thought! **


	4. On a Date

**Day 4: On a Date**

"Munchlax! Come back here!" May shouted, chasing after her pokemon.

"Munchmunch!" Munchlax cried as he ran down the sidewalk. He was hungry and searching for somewhere to get some food! He skidded to a stop before colliding in to Drew's leg. "Muuuuunch…"

"Munchlax…don't…run off…like that…" May panted, doubling over with her hands resting on her knees. When she caught her breath, she stood straight and noticed just whom Munchlax had crashed in to. "D-Drew…sorry about Munchlax." She apologized before sending the pokemon back into his pokeball.

"It's sad that your pokemon don't listen to you well enough to stay in their pokeballs, May." He criticized. "It really shows how bad a trainer you are." Just then, Roserade popped out of her ball.

"Roserade!" she called, poking her trainer in the side.

"Hey!" Drew blushed, jumping back slightly. May giggled at the display.

"Bad trainer, huh?" she snickered.

"Whatever…" Drew blushed. Roserade took their hands and started dragging them. "Roserade, w-what are you doing?" Drew stuttered, surprised by his partner's sudden take-charge attitude.

"What is she doing, Drew?" May asked.

"I-I don't know!" The two were pulled all the way to a set of picnic tables, instructed to sit before Roserade turned around, Beautifly and Blaziken popping out and following.

"Beautifly! Blaziken! Where're you going?" May asked frantically.

"Blay!"

"Beautiflyyy!"

The two disappeared with Roserade, leaving their trainers alone. "Well. That was certainly awkward…" Drew stated.

"Tell me about it. What has gotten into them?" May asked before stretching out on the table and releasing a yawn. Drew stared at her as she did this, a light blush taking over his cheeks. "Does Roserade do that often? Just take control of what ever you're doing?" May asked, snapping his attention back.

"Um. No, not normally…I don't know what they're doing…" Drew answered. Then, he noticed them coming back with…silver platters…

"What are you looking at…oh."

"Roserade." The flower pokemon stated, plunking down the platter in her petals. Beautifly and Blaziken copied before allowing themselves to all three be returned.

"What in the world could this be?" May asked, lifting the cover of one platter. Sandwiches? Under the other two was some sushi and desserts. "Why would they do this?"

Drew swallowed hard, maybe he shouldn't confide in his pokemon so much. "I-I have no idea…but I guess we shouldn't let this all go to waste? Whatever their reason, they worked hard to this…" he lied, hastily grabbing some of the food and turning away from the brunette.

**This is what happens with me…I completely forgot to do this, then I started procrastinating, then I lied to myself, then I finally did this. I have no idea if Drew is too OOC in this story or what, I just made him dorky.**

**Also, why no one but stocky-parker-dog reviewing?! This story has 336 views and only four reviews…this makes me incredibly sad.**

**Tomorrow's prompt: Kissing. Hehehehehe!**

**Please, review and tell me what you think!**


	5. Kissing

**Day 5: Kissing**

"You're so cute, Drew~" May cooed with giggle.

"Huh? What?" Drew stuttered, a blush covering his cheeks.

May nodded, giggling once more, "Yep, sometimes I just wanna give you a great big kiss!" she responded, leaping to her feet from her chair and taking Drew's (admittedly chubby) cheeks in her palms, leaning down to him…

"-ew…Drew! Dreeeeew, yoohoo! Earth to Drew!" May waved her hands frantically in the green-haired boy's face.

"Huhwah?!" Drew snapped out of his daze. May sat back down, releasing a held in sigh. "What happened?" he asked nervously.

"Uh…you were just daydreaming…and you started leaning toward me when I tried to snap you out of it…" she mumbled. Drew blinked, a blush forming truly on his face.

"O-oh…whoops…heh." He sweatdropped, trying to act cool. "Whatever, it was probably no big deal I mean I don't even remember what I was daydreaming about." He flicked his hair, "So, you wanna go get some ice-"

"You've been acting really weird lately…are you sure you're OK? I mean, you're not getting sick or anything, are you?" May stood and placed the back of her hand to Drew's forehead. "Hmm…" she pushed his hair up and kissed his forehead, trying to estimate a temperature.

"Wh-what are you doing?" Drew jerked back, causing May to fall forward and place her lips on his. Both of them froze, unsure what to do next or how to address what was happening. May eventually backed away, standing up tall. "U-um…I-I gotta go…uh…t-train o-or something…!" Drew stuttered and jumped up, taking his things and rushing out the door.

May stood quiet for a moment, processing what had just happened. "Uh! Drew!" she shouted and ran out after him only a few short moments after him. She ran out and found him crouched down next to a fence, glancing out at the lake like a calming remedy. "Drew…" May stooped down next to him. "I-I am really sorry about that I don't know what I was even doing but I mean you did lean back like that and I couldn't help my balance depending on you staying where you were but I mean, like-"

Drew cut her off with a kiss of his own. It was quick, just a small peck to get her to stop talking. "You talk way too much when you're nervous…"

May smiled, nudging him playfully, "You don't talk enough." He snickered; nodding and giving his attention back to the water. "Sooo…does this mean you like me?"

"You wish."

"Um-hmmm?"

Drew sighed, burying his face in his knees. "Yeah…I do. A lot." He blushed but hid it in his arms.

"Good, 'cause I like you, too." May pecked his cheek, smiling brightly.

Drew turned his head, keeping his cheek on knees and mumbling, "Really?"

"Really."

**I screwed up! I didn't do it yesterdaaaaaay! Ohhhhhh weeeeeeell!**

**They are officially together now! (Took 'em long enough but details)**

**Tomorrow's prompt: wearing each other's clothes. Do you guys have any ideas for this one? A reason why they'd be wearing the other's clothes?**

**Review and tell me what you thought!**


	6. Wearing each other's clothes

**Day 6: Wearing each other's clothes**

May threw open the bathroom door, sauntering out sporting new attire: Drew's purple vest and jeans, her hair now without it's normal bandana. She had Drew's dark shirt and held her hair back. "Look at me, I'm Drew Hayden and I like to think I'm _such_ a great coordinator." She snickered, gliding around the space of the Pokemon Center.

Drew huffed in annoyance before an idea suddenly hit him and jumped up, racing to the bathroom with a yellow bag in hand. He emerged a few minutes later in May's orange zip-up and black skirt with her green bandana tied awkwardly around his head. "I'm May Maple. Look at me as stuff my face with as much food as possible! Om. Nom. Nom." He came to her face, a mere two inches shorter.

May tried to hold back her laughter, but found it hard when even Drew was puffing his cheeks trying to keep the chortles down. She released the laughter, flopping on a couch and clutching her stomach. "Th-this is aw-awesome! Ohmygod!" she cried, burying her face in the cushions. Drew managed to work his laughing down and keep only a smile.

"C'mon, let's go change back…people are starting to stare…" He said, holding a hand out.

"That's probably because an eleven-year-old is wearing girls' clothes, Drew." May snickered, allowing him to help her up.

"Just shut up and go change" he whined, pushing her off on her way.

* * *

May came back into their room with Drew's vest still on. "So that's where it went…" he mumbled instead of a hello.

"You've got another one just like it, why do you need this one?" May asked, flopping onto the bed and allowing Skitty to curl up on her stomach.

"I just didn't know you took it. It's kinda cute on you…" Drew blushed, sitting on the bed and leaning over May's face, pecking her forehead.

"Kinda cute?!"

**May. Just take it. Take the compliment and run. Jeez…**

**This is one of the suckiest ones of these…Ah cain't dew eet!**

**Tomorrow's prompt: Cosplaying. What do you guys think they should cosplay as?**

**Review and tell me what you thought!**


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